Detergents Containing a 1,3-Diene Group in the Hydrophobic Segment. Facile Chemical Modification by a Diels-Alder Reaction with Hydrophilic Dienophiles in Aqueous Solution

Article abstract of DOI:10.1021/jo00164a006

The objective of this investigation is a series of 1,3-diene-containing detergents that may be converted into derivatives of relatively high monomeric aqueous solubility by a Diels-Alder reaction with hydrophilic dieniphiles under mild aqueous conditions.Triton X-100 analogue 10, sodium dodecadienyl sulfate 16, and dodecadienyl maltoside 18 were synthesized.Detergents 16 and 18 reacted rapidly with the potent hydrophilic triazolinedione dienophile 19 in aqueous solution at 25 deg C, forming the adducts 20 and 21 quantitatively.Diels-Alder adducts also formed readilybetween the three diene detergents and sulfophenyl maleimide 26, although the reaction rate was somewhat slower than that of 19.Diene detergent 18 led to a stable CHCl3-water emulsion while its Diels-Alder adduct did not.By monitoring the enzymatic activity of phospholipase A₂ and α-chymotrypsin as a function of added 19 both in the presence and absence of detergents, it was shown that 19 reacts preferentially with the 1,3-diene unit of the detergents rather than with the proteins.